Acetic Acid → HCID 67121146, compound

HRID 1510450Notes

Reaction equation

HRID 1510450 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([CH2:17][OH:18])[CH:13]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[Cl:19]N1C(=O)CCC1=O.S(=O)(=O)(O)O.[C:32]([OH:35])(=O)[CH3:33]>O>[C:32]([O:18][CH2:17][C:14]1[C:13]([Cl:19])=[C:12]([C:4]2[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:11])[F:10])=[C:2]([F:1])[CH:3]=2)[O:16][N:15]=1)(=[O:35])[CH3:33]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 31398ChlorosuccinimideHCID 67121090HCID 67121090, compound

Product 1

HCID 67121146HCID 67121146, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (5-(3-fluoro-4-(trifluoromethyl)phenyl)isoxazol-3-yl)methanol (1.4 g, 5.36 mmol) in acetic acid (12 mL), N-chlorosuccinimide (1.07 g, 8.04 mmol) and sulphuric acid (0.6 mL) were added. The reaction mixture was stirred for 5 hours at 120° C. before being allowed to cool and then diluted with water (100 mL). The aqueous reaction mixture was extracted with diethyl ether (3×100 mL), the organics combined, washed with brine, dried with Na2SO4. The volatiles were removed in vacuo and the resulting residue was purified by silica gel chromatography, eluting with heptane to 20% ethylacetate in heptane, to afford (4-chloro-5-(3-fluoro-4-(trifluoromethyl)phenyl)isoxazol-3-yl)methyl acetate (1 g, 2.96 mmol).

Workup

  1. temperatureto cool
  2. extractionThe aqueous reaction mixture was extracted with diethyl ether (3×100 mL)
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. customThe volatiles were removed in vacuo
  6. customthe resulting residue was purified by silica gel chromatography
  7. washeluting with heptane to 20% ethylacetate in heptane

Sources & evidence

ORD record
ord-ada0b27a3a714235bc43c4c5ead17415
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

Loading…